Biosynthetic Origin of the Carbon Skeleton and Nitrogen Atom of Pamamycin-607, a Nitrogen-Containing Polyketide

Hashimoto, Makoto; Komatsu, Haruhiko; Kozone, Ikuko; Kawaide, Hiroshi; Abé, Hiroshi; Natsume, Masahiro

doi:10.1271/bbb.69.315

Cited by 16 publications

(24 citation statements)

References 11 publications

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“…17) As a result, the following route was clarified: large and small hydroxy acids were synthesized first, the dimethylamino group was then introduced in the large hydroxy acid, and finally the macrodiolide ring was formed (Fig. 6).…”

Section: Biosynthesis Of Pamamycinmentioning

confidence: 99%

Studies on bioactive natural products involved in the growth and morphological differentiation of microorganisms

Natsume

2016

J. Pestic. Sci.

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Section: Biosynthesis Of Pamamycinmentioning

confidence: 99%

Studies on bioactive natural products involved in the growth and morphological differentiation of microorganisms

Natsume

2016

J. Pestic. Sci.

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“…Non-labeled and 13 C-labeled 5 were prepared by alkaline hydrolysis of non-labeled and 13 C-labeled pamamycin (1), respectively. 13 C-Labeled 1 was obtained by a feeding experiment with [2-13 C] acetate as described in a previous paper [8]. Hydroxy acid 5 was used as a mixture of homologues, and incubated for 60 hours.…”

Section: Biosynthetic Intermediates Produced By Mutants and The Wild mentioning

confidence: 99%

“…13 C-labeled 1 was obtained by a feeding experiment of [2-13 C] acetate in S. alboniger as previously described [8].…”

Section: Preparation Of Authentic Compounds For Lc-ms Analysis and Sumentioning

confidence: 99%

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Nitrogen Incorporation in the Biosynthetic Pathway of the Nitrogen-containing Polyketide, Pamamycin in Streptomyces alboniger

et al. 2005

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The biosynthetic pathway of pamamycin (1), a nitrogen-containing polyketide, was investigated using blocked mutants of Streptomyces alboniger. Hydroxy acids K (3), L (4) and S (5) were found in cultured materials of blocked mutants and the wild type strain, but no PM-ketone (2) was detected. Hydroxy acids 3, 4, 5 and de-Nmethylhydroxy acid L (7) were converted into 1, but 2 nor de-N-methylpamamycin (6) were not. We also confirmed that 3 and 7 were converted into 4. These results showed that an amino group was introduced into the carbonyl group of 3 by transamination, and subsequent Nmethylation led to 4 in the pamamycin biosynthetic pathway. Quantitative analyses of hydroxy acid intermediates 3, 4, and 5, and pamamycin (1) suggested that transamination was the rate-determining step in pamamycin biosynthesis.

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“…Aerial mycelium-inducing activity decreased by ca. 1/10 per methylene unit in the side chain.Keywords pamamycin, structure-activity relationship, aerial mycelium, differentiation, polyketide Pamamycins are unique polyketides containing a nitrogen atom [1,2]. Pamamycins were discovered as aerial mycelium-inducing substances of Streptomyces alboniger by McCann and Pogell [3], and their isolation and structural elucidation were accomplished by our group [4ϳ6].…”

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Structure-activity Relationship of Pamamycins: Effect of Side Chain Length on Aerial Mycelium-inducing Activity

et al. 2008

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Two pamamycin homologues with different side chain lengths were isolated from Streptomyces sp. HKI-0118. Aerial mycelium-inducing activity decreased by ca. 1/10 per methylene unit in the side chain.Keywords pamamycin, structure-activity relationship, aerial mycelium, differentiation, polyketide Pamamycins are unique polyketides containing a nitrogen atom [1,2]. Pamamycins were discovered as aerial mycelium-inducing substances of Streptomyces alboniger by McCann and Pogell [3], and their isolation and structural elucidation were accomplished by our group [4ϳ6]. Pamamycin-607 (3), a major active component with MW 607, induces or stimulates aerial mycelium formation and regulates secondary metabolite production in many Streptomyces spp. in addition to the species in which it is produced [7].We have examined the structure-activity relationship of pamamycins by isolating homologues [8,9] and de-Nmethyl derivatives from cultured material of S. alboniger [10,11] and by preparing derivatives [12]. We have determined that the nitrogenous group is indispensable to aerial mycelium-inducing activity, that de-N-methylation increases this activity 1.5 times, and that substitution of the methyl group at R 3 or R 4 with an ethyl group markedly lowers activity.To refine our understanding of the structure-activity relationship around the nitrogenous group, we planed to isolate homologues with different side chain lengths and to examine their aerial mycelium-inducing activity. There are two reports on such homologues: MS-282a and MS-282b were isolated from S. tauricus ATCC 27470 as inhibitors of calmodulin-activated myosin light chain kinase [13]. Härtl et al. reported the production of various lengths of the nitrogen-containing side chain of pamamycin (nϭ2ϳ4 in Fig. 1) by Streptomyces sp. HKI-0118 and S. aurantiacus IMET 43917 [14], but they were unsuccessful in isolating these components.We report the isolation of two pamamycin homologues, 1 and 2, with different side chain lengths from Streptomyces sp. HKI-0118 ( Fig. 1) and describe their aerial myceliuminducing activity.Streptomyces sp. HKI-0118 was cultured in 2.0-liter Erlenmeyer flasks containing 1.0 liter of glucose -oat meal -yeast extract medium [14] at 28°C for 7 days on a rotary shaker (150 rpm). The fermentation broth (26 liters) was separated into filtrate and mycelia, then the filtrate was treated with EtOAc at pH 8 and the mycelia were macerated in Me 2 CO. The Me 2 CO extract of mycelia was

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Biosynthetic Origin of the Carbon Skeleton and Nitrogen Atom of Pamamycin-607, a Nitrogen-Containing Polyketide

Cited by 16 publications

References 11 publications

Studies on bioactive natural products involved in the growth and morphological differentiation of microorganisms

Studies on bioactive natural products involved in the growth and morphological differentiation of microorganisms

Nitrogen Incorporation in the Biosynthetic Pathway of the Nitrogen-containing Polyketide, Pamamycin in Streptomyces alboniger

Structure-activity Relationship of Pamamycins: Effect of Side Chain Length on Aerial Mycelium-inducing Activity

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